U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C31H33F3N2O5S
Molecular Weight 602.664
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIPRANAVIR

SMILES

CCC[C@@]2(CCC1=CC=CC=C1)CC(O)=C([C@H](CC)C3=CC=CC(NS(=O)(=O)C4=NC=C(C=C4)C(F)(F)F)=C3)C(=O)O2

InChI

InChIKey=SUJUHGSWHZTSEU-FYBSXPHGSA-N
InChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16802849 | https://www.ncbi.nlm.nih.gov/pubmed/9719600 | http://adisinsight.springer.com/drugs/800008750

Tipranavir (PNU-140690, trade mark APTIVUS) is a potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class. Tipranavir has potent in vitro activity against a variety of HIV-1 laboratory strains and clinical isolates, including those resistant to ritonavir, as well as HIV-2. The drug is launched in several countries, including the US and in the EU. APTIVUS, co-administered with ritonavir, is indicated for combination antiretroviral treatment of HIV-1 infected patients who are treatment-experienced and infected with HIV-1 strains resistant to more than one protease inhibitor.

CNS Activity

CNS Non-penetrant
1014
Curator's Comment: Tipranavir do not reach therapeutical concentrations in CSF

Originator

Pfizer
420
Curator's Comment: # Pharmacia & Upjohn (now Pfizer)

Approval Year

2005
131
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 8.0 pM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
APTIVUS

Approved Use

APTIVUS, co-administered with ritonavir, is indicated for combination antiretroviral treatment of HIV-1 infected patients who are treatment-experienced and infected with HIV-1 strains resistant to more than one protease inhibitor (PI). This indication is based on analyses of plasma HIV-1 RNA levels in two controlled studies of APTIVUS/ritonavir of 48 weeks duration in treatment-experienced adults and one open-label 48-week study in pediatric patients age 2 to 18 years. The adult studies were conducted in clinically advanced, 3-class antiretroviral (NRTI, NNRTI, PI) treatment-experienced adults with evidence of HIV-1 replication despite ongoing antiretroviral therapy. The following points should be considered when initiating therapy with APTIVUS/ritonavir: The use of APTIVUS/ritonavir in treatment-naïve patients is not recommended [ see Warnings and Precautions (5.1)

Launch Date

1.1193984E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
77.6 μM
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FED
94.8 μM
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FED
135 μM
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
375 mg/m² 2 times / day steady-state, oral
dose: 375 mg/m²
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
710 μM × h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FED
851 μM × h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FED
1190 μM × h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
375 mg/m² 2 times / day steady-state, oral
dose: 375 mg/m²
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FED
5.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FED
8.1 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
375 mg/m² 2 times / day steady-state, oral
dose: 375 mg/m²
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Ritonavir
Ritonavir
 TIPRANAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
unhealthy, 18–65
n = 186
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 18–65
Sex: M+F
Population Size: 186
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
Disc. AE: Gastrointestinal disorder NOS, Gastrointestinal disorder NOS...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disorder NOS (grade 1, 1%)
Gastrointestinal disorder NOS (moderate, 2.1%)
Gastrointestinal disorder NOS (severe, 1%)
Transaminases increased (grade 1, 1%)
Transaminases increased (moderate, 1.6%)
Transaminases increased (severe, 4.8%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
1200 mg 2 times / day multiple, oral
Highest studied dose
Dose: 1200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15097154
Page: p.381
unhealthy, 35.2
n = 10
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 35.2
Sex: M+F
Population Size: 10
Sources:
https://pubmed.ncbi.nlm.nih.gov/15097154
Page: p.381
Sources:
https://pubmed.ncbi.nlm.nih.gov/15097154
Page: p.381
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Disc. AE: Hepatitis, Hepatic decompensation...
AEs leading to
discontinuation/dose reduction:
Hepatitis
Hepatic decompensation
Intracranial hemorrhage
Platelet aggregation
Coagulation abnormal
Diabetes mellitus
Hyperglycemia
Immune reconstitution syndrome
Fat redistribution
Lipids increased
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1, 5
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1, 5
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash (0.5%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1, 5
AEs

AEs

AESignificanceDosePopulation
Gastrointestinal disorder NOS grade 1, 1%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
unhealthy, 18–65
n = 186
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 18–65
Sex: M+F
Population Size: 186
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
Transaminases increased grade 1, 1%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
unhealthy, 18–65
n = 186
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 18–65
Sex: M+F
Population Size: 186
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
Transaminases increased moderate, 1.6%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
unhealthy, 18–65
n = 186
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 18–65
Sex: M+F
Population Size: 186
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
Gastrointestinal disorder NOS moderate, 2.1%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
unhealthy, 18–65
n = 186
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 18–65
Sex: M+F
Population Size: 186
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
Gastrointestinal disorder NOS severe, 1%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
unhealthy, 18–65
n = 186
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 18–65
Sex: M+F
Population Size: 186
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
Transaminases increased severe, 4.8%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
unhealthy, 18–65
n = 186
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 18–65
Sex: M+F
Population Size: 186
Sources:
https://pubmed.ncbi.nlm.nih.gov/26730818
Page: p.11
Coagulation abnormal Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Diabetes mellitus Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Fat redistribution Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Hepatic decompensation Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Hepatitis Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Hyperglycemia Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Immune reconstitution syndrome Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Intracranial hemorrhage Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Lipids increased Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Platelet aggregation Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1
Rash 0.5%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Co-administed with::
ritonavir, oral(200 mg, b.i.d.)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1, 5
unhealthy
Health Status: unhealthy
Condition: HIV-1 infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021814s011lbl.pdf
Page: p.1, 5
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

substrate
1737

inducer
781
inducer
389

inhibitor
1767
inhibitor
1852

substrate
1217
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP3A
214

P-gp
1461

CYP1A2
1524

CYP2C19
1478

OATP2B1
123

UGT enzymes
4

Ca2+ channels
57
P-gp
1537
P-gp
257

CYP1A2
701

UGT enzymes
2

CYP2C19
293
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 inconclusive
CYP2C19
1553
 inconclusive
CYP2C9
1819
 inconclusive
Ca2+ channels
60
 inconclusive
UGT enzymes
4
 inconclusive
UGT enzymes
4
 inconclusive
P-gp
1650
 likely
CYP2D6
1891
 moderate [IC50 16.3 uM]
yes (co-administration study)
Comment: coadministration with dextromethorphan led to potent inhibition of CYP2D5
Page: 100.0
CYP3A4
1925
 moderate
P-gp
1650
 weak
CYP2C9
1819
 yes [IC50 0.26 uM]
no (co-administration study)
Comment: coadministration with warfarin had no effect
Page: 100.0
CYP3A4
1925
 yes [IC50 2.3 uM]
CYP2C19
1553
 yes [IC50 2.7 uM]
CYP1A2
1692
 yes [IC50 >50 uM]
yes (co-administration study)
Comment: coadministration with caffeine led to moderate induction at steady state
Page: 100.0
CYP3A
298
 yes
OATP2B1
126
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
1217
 no
P-gp
1537
 yes
CYP3A4
1737
 yes
yes (co-administration study)
Comment: coadministration with ketaconazole inhibited the metabolism of tipranavir by 90%
Page: 96.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:63628
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63628
ChemicalBook
CB9501005
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9501005
MolPort
MolPort-003-850-561
https://www.molport.com/shop/molecule-link/MolPort-003-850-561
ZINC
ZINC000100016058
http://zinc15.docking.org/substances/ZINC000100016058
eMolecules
36754763
https://www.emolecules.com/cgi-bin/more?vid=36754763
PubMed

PubMed

TitleDatePubMed
Structure-based design of HIV protease inhibitors: sulfonamide-containing 5,6-dihydro-4-hydroxy-2-pyrones as non-peptidic inhibitors.
1996 Oct 25
Antiviral activity of the dihydropyrone PNU-140690, a new nonpeptidic human immunodeficiency virus protease inhibitor.
1997 May
In vitro combination of PNU-140690, a human immunodeficiency virus type 1 protease inhibitor, with ritonavir against ritonavir-sensitive and -resistant clinical isolates.
1997 Nov
Tipranavir (PNU-140690): a potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class.
1998 Aug 27
Tipranavir inhibits broadly protease inhibitor-resistant HIV-1 clinical samples.
2000 Sep 8
Analysis of protease inhibitor combinations in vitro: activity of lopinavir, amprenavir and tipranavir against HIV type 1 wild-type and drug-resistant isolates.
2004 Mar
Design of HIV-1 protease inhibitors active on multidrug-resistant virus.
2005 Mar 24
Selection and characterization of HIV-1 showing reduced susceptibility to the non-peptidic protease inhibitor tipranavir.
2005 Oct
Tipranavir: PNU 140690, tipranivir.
2006
Susceptibility to protease inhibitors in HIV-2 primary isolates from patients failing antiretroviral therapy.
2006 Apr
Tipranavir: the first nonpeptidic protease inhibitor for the treatment of protease resistance.
2007 Nov
Tipranavir: a new option for the treatment of drug-resistant HIV infection.
2007 Sep 15
Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization.
2007 Sep 28
Characterization of a novel human immunodeficiency virus type 1 protease inhibitor, A-790742.
2008 Apr
Intracranial hemorrhage and liver-associated deaths associated with tipranavir/ritonavir: review of cases from the FDA's Adverse Event Reporting System.
2008 Nov
Hepatic profile analyses of tipranavir in Phase II and III clinical trials.
2009 Dec 14
Cytotoxicological analysis of a gp120 binding aptamer with cross-clade human immunodeficiency virus type 1 entry inhibition properties: comparison to conventional antiretrovirals.
2009 Jul
Novel protease inhibitors (PIs) containing macrocyclic components and 3(R),3a(S),6a(R)-bis-tetrahydrofuranylurethane that are potent against multi-PI-resistant HIV-1 variants in vitro.
2010 Aug
Evaluating the substrate-envelope hypothesis: structural analysis of novel HIV-1 protease inhibitors designed to be robust against drug resistance.
2010 May
In vitro activity of antiretroviral drugs against Plasmodium falciparum.
2011 Nov
Activity of human immunodeficiency virus type 1 protease inhibitors against the initial autocleavage in Gag-Pol polyprotein processing.
2012 Jul
Novel method to assess antiretroviral target trough concentrations using in vitro susceptibility data.
2012 Nov
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
GRL-0519, a novel oxatricyclic ligand-containing nonpeptidic HIV-1 protease inhibitor (PI), potently suppresses replication of a wide spectrum of multi-PI-resistant HIV-1 variants in vitro.
2013 May
P2' benzene carboxylic acid moiety is associated with decrease in cellular uptake: evaluation of novel nonpeptidic HIV-1 protease inhibitors containing P2 bis-tetrahydrofuran moiety.
2013 Oct
Substrate envelope-designed potent HIV-1 protease inhibitors to avoid drug resistance.
2013 Sep 19
Patents

Patents

20010044451
26
JP2006511554A
19
JP2006512339A
22
JP2007516260A
16
JP2007536237A
19
JP2009525265A
19
JP2009531441A
18
JP2010521465A
6
JP2011508747A
61
JP2011508748A
29
JP4676536B2
28
JP4738172B2
28

Sample Use Guides

In Vivo Use Guide
Adults: 500 mg APTIVUS® (tipranavir), co-administered with 200 mg ritonavir, twice daily. Pediatric patients (age 2 to 18 years): Dosing is based on body weight or body surface area not to exceed adult dose.
Route of Administration: Oral
In Vitro Use Guide
Tipranavir inhibits the replication of laboratory strains of HIV-1 and clinical isolates in acute models of T-cell infection, with EC50 ranging from 0.03 to 0.07 µM (18-42 ng/mL)
Name Type Language
TIPRANAVIR
EMA EPAR   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
3'-((1R)-1-((6R)-5,6-DIHYDRO-4-HYDROXY-2-OXO-6-PHENETHYL-6-PROPYL-2H-PYRAN-3-YL)PROPYL)-5-(TRIFLUOROMETHYL)-2-PYRIDINESULFONANILIDE
Systematic Name English
TIPRANAVIR [MART.]
Common Name English
TIPRANAVIR [EMA EPAR]
Common Name English
TIPRANAVIR [ORANGE BOOK]
Common Name English
APTIVUS
Brand Name English
tipranavir [INN]
Common Name English
Tipranavir [WHO-DD]
Common Name English
TIPRANAVIR [VANDF]
Common Name English
TIPRANAVIR [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000246
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
NCI_THESAURUS C97366
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
EMA ASSESSMENT REPORTS APTIVUS (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
WHO-VATC QJ05AE09
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
LIVERTOX NBK548389
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
WHO-ATC J05AE09
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
NDF-RT N0000175889
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
Code System Code Type Description
RXCUI
190548
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY RxNorm
CHEBI
63628
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
CAS
174484-41-4
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
SMS_ID
100000085237
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
WIKIPEDIA
TIPRANAVIR
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
PUBCHEM
54682461
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
MESH
C107201
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
LACTMED
Tipranavir
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
FDA UNII
ZZT404XD09
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
DAILYMED
ZZT404XD09
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
HSDB
8083
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
MERCK INDEX
m10885
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL222559
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
EVMPD
SUB04883MIG
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID6048622
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
NCI_THESAURUS
C66603
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
DRUG BANK
DB00932
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
DRUG CENTRAL
3609
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
INN
7774
Created by admin on Fri Dec 15 16:26:43 UTC 2023 , Edited by admin on Fri Dec 15 16:26:43 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of TIPRANAVIR
SALT/SOLVATE (PARENT)
Structure of TIPRANAVIR DISODIUM
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966